Synthesis of the Major Oxepane Segment of Zoapatanol

Abstract

A linear synthesis of the major oxepane fragment of zoapatanol, showing the induction of uterine contractions, and cervical dilation and uterine bleeding (by the concentrated zoapatle tea) in early human pregnancy, isolated from the leaves of Mexican zoapatle plant Montanoa tomentosa, is described from known intermediate involving Sharpless asymmetric epoxidation, bis-epoxide opening reaction with Corey-Chaykovsky reagent, ring-closing metathesis reaction, and Horner-Wadsworth-Emmons olefination reaction as key steps.